Water → Pyrrolidine, 1-(6-chloro-3,4-dihydro-2-naphthalenyl)-

HRID 1639355Notes

Reaction equation

HRID 1639355 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 521998p-Toluenesulfonic acid monohydrateHCID 44561396-Chloro-2-tetralone

Product 1

HCID 10444008Pyrrolidine, 1-(6-chloro-3,4-dihydro-2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1155 g (6.4 mol) of 6-chloro-3,4-dihydro-2(1H)-naphthalenone are dissolved in 5 l of toluene, 500 g (7.0 mol) of pyrrolidine and subsequently a solution of 26 g (0.14 mol) of p-toluenesulfonic acid monohydrate in toluene are added dropwise thereto and the mixture is boiled under reflux on a water separator. When about 120 ml of water have separated, 4 l of toluene are distilled and the mixture is left to cool slowly. A solid thereby crystallizes out. Filtration and washing with acetone gives 1-(6-chloro-3,4-dihydro-2-naphthyl)-pyrrolidine with melting point 117°-118°. Concentration of the mother liquor, suspension of the residue in ether, filtration and washing with acetone gives an additional portion of the above product with melting point 117°-118°.

Workup

  1. customWhen about 120 ml of water have separated
  2. distillation4 l of toluene are distilled
  3. waitthe mixture is left
  4. temperatureto cool slowly
  5. customA solid thereby crystallizes out
  6. filtrationFiltration
  7. washwashing with acetone

Sources & evidence

ORD record
ord-34ca0f2bb3bf4a8bb2efdbecc191d599
Source dataset
uspto-grants-1989_11
Patent number
US04883815

Reaction notes

Loading…